Synthesis and antiproliferative activity of some novel derivatives of diospyrin, a plant-derived naphthoquinonoid

Madhushree Das Sarma; Rina Ghosh; Amarendra Patra; Banasri Hazra

doi:10.1016/j.bmc.2007.03.050

Synthesis and antiproliferative activity of some novel derivatives of diospyrin, a plant-derived naphthoquinonoid

Bioorg Med Chem. 2007 Jun 1;15(11):3672-7. doi: 10.1016/j.bmc.2007.03.050. Epub 2007 Mar 18.

Authors

Madhushree Das Sarma¹, Rina Ghosh, Amarendra Patra, Banasri Hazra

Affiliation

¹ Department of Pharmaceutical Technology, Jadavpur University, Calcutta 700 032, India.

PMID: 17400463
DOI: 10.1016/j.bmc.2007.03.050

Abstract

Derivatisation of diospyrin, a bisnaphthoquinonoid isolated from Diospyros montana Roxb., led to the modification of its inhibitory activity, in vitro, towards a murine tumour model, Ehrlich ascites carcinoma (EAC), and two human cancer cell lines, viz., malignant skin melanoma (A375) and epidermoid laryngeal carcinoma (Hep2). Among the novel derivatives, an epoxide exhibited the maximum antiproliferative activity (IC(50) values in the range of 0.03-0.21 microM) and a comparatively lower toxicity (IC(50) approximately 98 microM) in normal human peripheral blood mononuclear cells (PBMC). This compound might provide a novel 'lead' for the development of clinically effective antiproliferative agents against cancer.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry*
Antineoplastic Agents / pharmacology*
Cell Proliferation / drug effects*
Diospyros / chemistry
Disease Models, Animal
Humans
Inhibitory Concentration 50
Leukocytes, Mononuclear / drug effects
Mice
Naphthoquinones / chemical synthesis
Naphthoquinones / chemistry*
Naphthoquinones / pharmacology*
Plant Bark / chemistry
Tumor Cells, Cultured

Substances

Antineoplastic Agents
Naphthoquinones
diospyrin